[Poker_is_Hard]

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The National Football League Hall of Fame? For PLAYING accomplishments? Without regard to opportunity cost of the money or likelihood that you can get paid, I'd put it in the 400-1 or so range. He's 26 years old. He still has the time to do it. He's not ridiculously bad. Something could click. If it does, and he gets to stay with the Bears, then he might see a lot of playoff time. Big playoff wins will improve his stock even if he isn't quite as good as others. The Bears look likely to be a frequent playoff team in the near future at least. No methodology behind the guess.

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He would need to be inducted into the NFL HOF. The bet would pay off on his induction or the date he's eligibility expires.

Of course if he retires with zero realistic chance the bet will also be settled.